Two days after the aforementioned press conference, this reporter sat down with Diaz for what was supposed to be a wide-ranging interview. But it didn’t work out that way. I started by asking the candidate — who was recently an unenrolled voter — about her time as an independent. “I don’t know when it happened,” Diaz said. “You know, I was always a Republican at heart. I don’t exactly know why I changed, but I did, and then I changed back [to the GOP].” Next up was crime, which Diaz obviously intends to make a focus of her campaign. (Almost half of Boston’s murders occur in the Second Suffolk, Diaz frequently notes.) How might Diaz manage the problem differently from Wilkerson? “You know, I think a faith-based approach is always a good, um, process,” she answered. “I think right now, I don’t want to tip my hand too much. I do want to keep talking to the neighborhood — constituents. I have ideas, but I don’t exactly want to push them upon people.”
And so it went. We moved on to education, another subject close to Diaz’s heart. (Instead of attending her Dorchester elementary school, Diaz trekked to Melrose as a METCO student; her five-year-old daughter currently attends a Boston public school.) Diaz criticized Wilkerson for being beholden to the teachers’ unions and hinted at favoring charter schools, although she never used the phrase. She also said she’d like to make some changes involving food options in public schools. Care to elaborate on any of these? “No,” she said. “That’s good for now.” Later, discussing her previous support for Wilkerson — she actually volunteered for the senator’s 2002 campaign — Diaz mentioned that the senator “knows some people in my family.” Who, exactly? “People.”
All of which raises the question: who’s holding Diaz’s tongue? The circumstantial evidence points to Dan Winslow, former chief legal counsel for Governor Mitt Romney and now an attorney in the Boston office of Duane Morris. In a Globe story on Diaz earlier this year, Winslow explained that, after meeting her at a Tufts-alumni event, he urged her to run as a Republican. (Diaz has bachelor’s and master’s degrees in computer science from Tufts and just finished her second year at New England School of Law.) Both Diaz and Winslow have said that she was already considering running before their chance encounter. And Diaz told the Phoenix that, even if she hadn’t connected with Winslow, she’d be running under the GOP banner.
All that may be true. Still, it’s hard not to see the Diaz campaign as a political version of Pygmalion, with Diaz, the unformed electoral neophyte, being molded by a canny political veteran. Heidi Ebert, Diaz’s press coordinator, is Winslow’s assistant at Duane Morris. And Ellen Schneider, Diaz’s campaign manager, worked with Winslow in the governor’s office and says she knows him well. (Asked by the Phoenix how she and Schneider connected, Diaz said someone had recommended her. Who? “I can’t remember, honestly.”)
For his part, Winslow insists that — other than providing legal advice — his role in the Diaz campaign is peripheral. “She’s the candidate; I’m not the candidate,” he says. “She’s doing great on her own. I’d like to help, but my help is completely inconsequential.” He also claims that Diaz has great political promise: “I’ve worked with a lot of candidates. And although she’s still a newly minted candidate, she probably is one of the most impressive individuals I’ve worked with in public life.”
